Zhou Leijie, Yuan Chunhao, Zeng Yuan, Liu Honglei, Wang Chang, Gao Xing, Wang Qijun, Zhang Cheng, Guo Hongchao
Department of Applied Chemistry , China Agricultural University , Beijing 100193 , China . Email:
Chem Sci. 2018 Jan 5;9(7):1831-1835. doi: 10.1039/c7sc04515h. eCollection 2018 Feb 21.
Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with -sulfonylimines for the synthesis of 1,2,3,6-tetrahydropyridines is developed. The reaction proceeds smoothly under mild reaction conditions to give the annulation products in moderate to excellent yields. Mechanistic exploration of this new annulation shows that the δ-sulfonamido-substituted enone and the -sulfonylimine serve as C5 and C1 synthons to furnish the annulation, respectively. Using chiral phosphine as the catalyst, an asymmetric variant of the model reaction gave the chiral product in up to 73% ee.
开发了膦催化的δ-磺酰胺基取代烯酮与-磺酰亚胺的[5+1]环化反应，用于合成1,2,3,6-四氢吡啶。该反应在温和的反应条件下顺利进行，以中等至优异的产率得到环化产物。对这种新环化反应的机理探索表明，δ-磺酰胺基取代烯酮和-磺酰亚胺分别作为C5和C1合成子来实现环化。使用手性膦作为催化剂，该模型反应的不对称变体以高达73%的对映体过量得到手性产物。
